US5480960A - Process for the preparation of an acid functional polyester resin - Google Patents

Process for the preparation of an acid functional polyester resin Download PDF

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Publication number
US5480960A
US5480960A US08/274,949 US27494994A US5480960A US 5480960 A US5480960 A US 5480960A US 27494994 A US27494994 A US 27494994A US 5480960 A US5480960 A US 5480960A
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United States
Prior art keywords
primary
compound
tertiary aliphatic
functional polyester
polyester resin
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Expired - Lifetime
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US08/274,949
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English (en)
Inventor
Jan Freriks
Pieter Groenveld
Petrus G. Kooijmans
Werner T. Raudenbush
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Hexion Inc
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Shell Oil Co
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Assigned to WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT reassignment WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT SECURITY AGREEMENT Assignors: BORDEN CHEMICAL, INC., RESOLUTION PERFORMANCE PRODUCTS LLC, RESOLUTION SPECIALTY MATERIALS LLC
Assigned to JPMORGAN CHASE BANK, N.A. AS COLLATERAL AGENT reassignment JPMORGAN CHASE BANK, N.A. AS COLLATERAL AGENT SECURITY AGREEMENT Assignors: HEXION SPECIALTY CHEMICALS, INC.
Assigned to JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT reassignment JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT SECURITY AGREEMENT Assignors: HEXION SPECIALTY CHEMICALS, INC.
Assigned to WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT reassignment WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT SECURITY AGREEMENT Assignors: HEXION SPECIALTY CHEMICALS, INC.
Assigned to RESOLUTION PERFORMANCE PRODUCTS LLC reassignment RESOLUTION PERFORMANCE PRODUCTS LLC RELEASE OF SECURITY INTEREST Assignors: GENERAL ELECTRIC CAPITAL CORPORATION
Assigned to WILMINGTON TRUST FSB, AS COLLATERAL AGENT reassignment WILMINGTON TRUST FSB, AS COLLATERAL AGENT SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BORDEN CHEMICAL FOUNDRY, LLC, BORDEN CHEMICAL INTERNATIONAL, INC., BORDEN CHEMICAL INVESTMENTS, INC., HEXION CI HOLDING COMPANY (CHINA) LLC, HEXION SPECIALTY CHEMICALS, INC., HEXION U.S. FINANCE CORP., HSC CAPITAL CORPORATION, LAWTER INTERNATIONAL INC., OILFIELD TECHNOLOGY GROUP, INC.
Assigned to JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT reassignment JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT SECURITY AGREEMENT Assignors: BORDEN CHEMICAL FOUNDRY, LLC, BORDEN CHEMICAL INTERNATIONAL, INC., BORDEN CHEMICAL INVESTMENTS, INC., HEXION CI HOLDING COMPANY (CHINA) LLC, HEXION LLC, HEXION SPECIALTY CHEMICALS, INC., HEXION U.S. FINANCE CORP., HSC CAPITAL CORPORATION, LAWTER INTERNATIONAL INC., OILFIELD TECHNOLOGY GROUP, INC.
Assigned to RESOLUTION PERFORMANCE PRODUCTS CORP reassignment RESOLUTION PERFORMANCE PRODUCTS CORP CERTIFICATE OF CONVERSION Assignors: RESOLUTION PERFORMANCE PRODUCTS LLC
Assigned to N SPECIALTY CHEMICALS, INC. reassignment N SPECIALTY CHEMICALS, INC. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: RESOLUTION PERFORMANCE PRODUCTS CORP
Assigned to MOMENTIVE SPECIALTY CHEMICALS INC. reassignment MOMENTIVE SPECIALTY CHEMICALS INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: HEXION SPECIALTY CHEMICALS, INC.
Assigned to HEXION SPECIALTY CHEMICALS, INC. reassignment HEXION SPECIALTY CHEMICALS, INC. CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY NAME PREVIOUSLY RECORDED ON REEL 027805, FRAME 0642. Assignors: RESOLUTION PERFORMANCE PRODUCTS CORP
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Assigned to JPMORGAN CHASE BANK, N.A. reassignment JPMORGAN CHASE BANK, N.A. PATENT SECURITY AGREEMENT Assignors: MOMENTIVE SPECIALTY CHEMICALS INC.
Anticipated expiration legal-status Critical
Assigned to HEXION INC. reassignment HEXION INC. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: WILMINGTON TRUST COMPANY
Assigned to BORDEN CHEMICAL FOUNDRY, LLC, HEXION U.S. FINANCE CORP., HSC CAPITAL CORPORATION, LAWTER INTERNATIONAL INC., OILFIELD TECHNOLOGY GROUP, INC., HEXION INC. (FORMERLY KNOWN AS HEXION SPECIALTY CHEMICALS INC.), HEXION INTERNATIONAL INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INTERNATIONAL INC.), HEXION INVESTMENTS INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INVESTMENTS, INC.), HEXION CI HOLDING COMPANY (CHINA) LLC reassignment BORDEN CHEMICAL FOUNDRY, LLC RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: WILMINGTON TRUST, NATIONAL ASSOCIATION (SUCCESSOR BY MERGER TO WILMINGTON TRUST FSB), AS COLLATERAL AGENT
Assigned to HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.) reassignment HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.) RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (030146/0970) Assignors: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints

Definitions

  • the present invention relates to a process for the preparation of a linear tertiary aliphatic carboxyl functional polyester resin, to a linear tertiary aliphatic carboxyl functional polyester resin obtainable by said process, to a polyglycidylester resin obtainable by glycidating said linear tertiary aliphatic carboxyl functional polyester resin and to powder coating compositions comprising said linear tertiary aliphatic carboxyl functional polyester resin or said polyglycidylester resin.
  • Powder coating compositions based on the solid reaction products of 2,2-bis-(4-hydroxyphenyl)propane and epichlorohydrin have been known for a long time. However, they show only minor ultraviolet resistance and are therefore not suitable for applications requiring a high outdoor durability such as automotive topcoats.
  • Triglycidylesters which can be used in outdoor durable coatings and in casting compositions are disclosed in U.S. Pat. No. 5,138,078. Due to the secondary nature of the terminal carboxyl functions present in the tricarboxylic acid adduct precursors, strongly alkaline conditions should be avoided during glycidation of these tricarboxylic acid adducts. As a result the triglycidylester produced will contain a relatively high level of hydrolyzable chlorine. In example 2 of U.S. Pat. No. 5,138,078 which relates to the glycidation of the 2:1 adduct of hexahydrophthalic anhydride and dimethylolpropionic acid, the product obtained has a chlorine content of 1.5%. Such a high level of residual chlorine is generally undesirable in coating compositions. In addition, the triglycidylesters reported in U.S. Pat. No. 5,138,078 are liquid, they can not be applied in powder coating compositions.
  • TGIC polyester/triglycidylisocyanurate
  • At least one diol compound C comprising two aliphatic hydroxyl groups which may each independently be a primary or a secondary hydroxyl group and
  • At least one dihydroxymonocarboxylic acid compound D comprising a tertiary aliphatic carboxyl group and two aliphatic hydroxyl groups, which may each independently be primary or secondary hydroxyl,
  • X ranges from 2 to 8
  • Y ranges from 2-N to 8.
  • reaction is continued until essentially all the nontertiary carboxyl groups initially present in the reaction mixture have been reacted.
  • the linear tertiary aliphatic carboxyl functional polyester resin produced according to the process of the invention is essentially free from nontertiary carboxyl groups when it has an acid value which substantially corresponds to the theoretical acid value calculated on the basis of the amount of tertiary carboxyl groups of the reactants as initially present in the reaction mixture.
  • the term "substantially” is used herein to indicate a deviation from the theoretical value of +/-5% at most. This is determined by standard alkali metric titration.
  • the molecular weight distribution and number average molecular weight of the resin produced will depend on the specific reactants and the ratios applied in the process of the invention.
  • the tertiary aliphatic carboxyl groups present in compounds A" and D practically do not react under the esterification conditions employed, glycidation of these tertiary aliphatic carboxyl groups with epihalohydrin can be performed under standard alkaline conditions whereby a polyglycidylester resin can be obtained which contains a low hydrolyzable halogen content, usually lower than about 0.5% by weight based on the total weight of the composition.
  • the process of the present invention may be carried out according to conventional esterification methods, preferably by azeotropic condensation.
  • the condensation is carried out by charging the compounds A to D simultaneously to the reactor whereafter the temperature is increased from room temperature to from about 200° to about 220° C. during a period of about 6 to about 8 hours, thus allowing the reaction to initiate and to proceed under continuous azeotropic removal of water.
  • the azeotropic removal of water is continued until a reaction product is obtained which has an acid value corresponding to the theoretical acid value as referred to above.
  • esterification catalyst such as for example dibutyltinoxide, paratoluenesulfonic acid, tinoctoate, zincoctoate and lithiumricinoleate may be used in the esterification process.
  • Preferable alcohol compounds A' for use in the process of the present invention are aliphatic and cycloaliphatic alcohols having one primary or one secondary hydroxyl group and having of from 1 to 6 carbon atoms, such as for example methanol, isopropanol, neopentanol, 2-butanol and cyclohexanol.
  • Suitable alcohol compounds A" are aliphatic and cycloaliphatic alcohols having one primary or one secondary hydroxyl group and having of from 1 to 6 carbon atoms and having in addition one tertiary aliphatic carboxyl group such as for example cyclohexane-1-methyl-4-hydroxy carboxylic acid and hydroxypivalic acid. Hydroxypivalic acid is a particularly preferred compound A".
  • Preferable compounds B for use in the process of the present invention are for example phthalic acid (PA), tetrahydrophthalic acid, hexahydrophthalic acid (HHPA), methylhexahydrophthalic acid, terephthalic acid, isophthalic acid, endomethylenetetrahydrophthalic acid, methylendomethylenetetrahydrophthalic acid, 1,4-cyclohexanedicarboxylic acid and 1,3-cyclohexanedicarboxylic acid or combinations thereof; HHPA being particularly preferred.
  • Preferable compounds C for use in the process of the present invention include branched aliphatic-, cycloaliphatic-, or araliphatic compounds, containing two aliphatic hydroxyl groups, each individually being either a primary or a secondary hydroxyl group, such as for example propylene glycol, neopentylglycol, hydrogenated diphenylolpropane (HDPP), hydrogenated 4,4'-dihydroxydiphenyl, 1,4-cyclohexanedimethylol, 1,4-dihydroxycyclohexane, hydroxypivalylhydroxypivalate and 2-butyl-2-ethyl-1,3-propanediol or mixtures thereof; HDPP being particularly preferred.
  • a typical example of a suitable compound D for use in the process of the present invention is dimethylolpropionic acid.
  • linear tertiary aliphatic carboxyl functional polyester resin obtainable according to the process of the present invention can be easily converted to a polyglycidylester resin according to methods known in the art i.e. by reaction with an excess epihalohydrin in the presence of a suitable base and catalyst. Most conveniently epichlorohydrin is being used.
  • linear tertiary aliphatic carboxyl functional polyester resin and the polyglycidylester resin of the invention are both suitable for use in powder coating compositions, which in the cured state show good outdoor durability. Moreover in view of the polymeric nature of the polyglycidylester resin of the invention a lower level of toxicity as compared to TGIC is foreseen and therefore they can advantageously be used as an alternative to TGIC in powder coatings.
  • the curable powder coating compositions of the invention may be prepared by addition of a cross-linking resin to either the linear tertiary aliphatic carboxyl functional polyester resin obtainable by the process of the present invention or to the polyglycidylester resin obtainable by glycidating said linear tertiary aliphatic carboxyl functional polyester resin.
  • the amount of cross-linking compound used in the powder coating compositions of the invention will normally be such so as to provide about equal amounts of reactive groups of the cross-linking compound and of the tertiary aliphatic carboxyl groups present in the linear tertiary aliphatic carboxyl functional polyester resin or of the epoxy groups present in the polyglycidylester resin.
  • Preferable cross-linking resins for use in combination with the linear tertiary aliphatic carboxyl functional polyester resins of the present invention are for example outdoor durable epoxy resins, such as for example the diglycidylester of terephthalic acid, the polyglycidylester resins according to the present invention, the diglycidylesters of alpha, alpha'-dibranched dicarboxylic acids as disclosed in European Patent Application publication number 518,408 and the polyglycidylesters based on polycarboxylic acids carrying two alkyl substituents on each of the alpha carbon atoms as disclosed in European patent application publication number 366,205.
  • outdoor durable epoxy resins such as for example the diglycidylester of terephthalic acid, the polyglycidylester resins according to the present invention, the diglycidylesters of alpha, alpha'-dibranched dicarboxylic acids as disclosed in European Patent Application publication number 518,408 and the polyglycidy
  • Preferable cross-linking resins for use in combination with the polyglycidylester resins of the present invention are for example the (corresponding) acid functional polyester resin of the present invention; solid polyacids such a sebacic acid, adipic acid, 1,12-dodecanedioic acid; anhydrides such as polyazeleic polyanhydride and trimellitic anhydride; acid functional polyesters such as the reaction product of one mole of trimethylopropane and 3 moles of hexahydrophtalic anhydride, the reaction product of 1-hexanediol with a molar excess of 1,12-dodecanedioic acid and the reaction product of one mole of hexamethoxymethylmelamine and 3 moles of hydroxypivalic acid; cyanuric acid; and solid basic curing agents such as dicyandiamide and BF 3 -complexes.
  • solid polyacids such as sebacic acid, adipic acid, 1,12
  • the powder coating compositions of the present invention may further comprise a catalyst and optionally other additives, as known in the art to be suitable for use in powder coating compositions.
  • Suitable catalyst are for example quaternary ammonium and phosphonium salts: metal salts/compounds such as for example stannous(II)octoate; basic compounds such as for example the imidazoles; and tertiary amines such as for example diazabicycloundecene.
  • the catalyst is typically present in an amount of from about 0.1 to about 2% by weight based on the weight of the total powder coating composition.
  • Suitable cure times and cure temperatures of the powder coating compositions of the invention are those conventionally applied in connection with powder coating systems.
  • the mixture was then heated to 150° C. in 30 minutes and xylene was added (5% weight on the total weight of the reaction mixture).
  • the temperature of the reaction mixture was increased in two hours to 210° C. and kept at 210° C. until the theoretical acid value as referred to above was reached.
  • the acid functional polyester thus formed was discharged and allowed to cool down to room temperature.
  • the organic phase was vacuum flashed to remove water, IPA and ECH.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Epoxy Resins (AREA)
  • Paints Or Removers (AREA)
US08/274,949 1993-07-15 1994-07-14 Process for the preparation of an acid functional polyester resin Expired - Lifetime US5480960A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP93202081 1993-07-15
EP93202081 1993-07-15

Publications (1)

Publication Number Publication Date
US5480960A true US5480960A (en) 1996-01-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
US08/274,949 Expired - Lifetime US5480960A (en) 1993-07-15 1994-07-14 Process for the preparation of an acid functional polyester resin

Country Status (7)

Country Link
US (1) US5480960A (de)
EP (1) EP0634434B1 (de)
JP (1) JP3432278B2 (de)
KR (1) KR100327917B1 (de)
CA (1) CA2127966A1 (de)
DE (1) DE69429746T2 (de)
TW (1) TW315376B (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5739213A (en) * 1995-01-06 1998-04-14 Shell Oil Company Acid functional and epoxy functional polyester resins
US6107442A (en) * 1997-02-21 2000-08-22 Shell Oil Company Outdoor durable coating compositions and acid functional polyester resins and polyglycidyl esters thereof usable therefor
US6187875B1 (en) 1997-03-25 2001-02-13 Shell Oil Company Acid functional polyester resins and lower temperature curable powder coating compositions comprising them
WO2010121392A1 (en) * 2009-04-21 2010-10-28 Dow Global Technologies Inc. Thermosettable composition containing a half ester of a cycloaliphatic diol and a thermoset product therefrom

Families Citing this family (15)

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Publication number Priority date Publication date Assignee Title
NZ334764A (en) * 1996-11-25 2000-01-28 Shell Int Research Acid functional and epoxy functional polyester resins
US6201073B1 (en) * 1996-12-02 2001-03-13 Shell Oil Company Tertiary carboxyl-functional polyester derived from cyclohexane dicarboxylic acid and dihydroxymono carboxylic acid
KR100515390B1 (ko) * 1996-12-30 2006-03-17 주식회사 케이씨씨 저온 경화형 수지 제조방법 및 이를 함유한 분체도료 조성물
NZ336654A (en) * 1997-02-21 2000-04-28 Shell Int Research Outdoor durable coating compositions and acid functional polyester resins and polyglycidal esters and use thereof
BR9808045A (pt) * 1997-03-25 2000-03-08 Shell Int Research Resinas de poliéster carboxil-funcional, e de poliglicidiléster linear ou ramificado, e , composição de revestimento em pó.
US6143838A (en) * 1997-03-25 2000-11-07 Shell Oil Company Acid functional and epoxy functional polyester resins
BE1011737A3 (fr) * 1998-02-09 1999-12-07 Ucb Sa Polyester contenant des groupes carboxyle tertiaires, son procede de preparation et compositions thermodurcissables en poudre le contenant.
JP2000063484A (ja) * 1998-04-07 2000-02-29 Yuka Shell Epoxy Kk エポキシ官能性ポリエステル樹脂の低粘度組成物
US6262186B1 (en) 1998-05-11 2001-07-17 Shell Oil Company Isocyanate-modified epoxy-functional polyester with crosslinking agent
US6103835A (en) * 1998-11-11 2000-08-15 Shell Oil Company Epoxy-functional polyester advanced with carboxyl-functional polyester or dicarboxylic acid (anhydride)
ES2215272T3 (es) * 1998-11-30 2004-10-01 Resolution Research Nederland B.V. Resinas de poliester con funcion acido y composiciones de revestimiento en polvo curables a temperaturas bajas que contienen dichas resinas.
US6388024B1 (en) 1999-10-29 2002-05-14 Ronald Petrus Clemens Van Gaalen Acid functional and epoxy functional polyester resins
US6451929B1 (en) 1999-10-29 2002-09-17 Resolution Performance Products, Llc Glycidyl ester by reacting COOH polyester with epihalohydrin
EP1621565A1 (de) * 2004-07-28 2006-02-01 Cytec Surface Specialties Austria GmbH Epoxidharz mit verbesserten elastischen Eigenschaften
JP3959092B2 (ja) 2004-12-27 2007-08-15 住化バイエルウレタン株式会社 ポリウレタン成形品およびその製造方法

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US3404018A (en) * 1965-09-27 1968-10-01 Celanese Coatings Co Esters of polyepoxides and hydroxycarboxylic acids
US3651098A (en) * 1968-01-29 1972-03-21 Ciba Ltd Polyglycidyl esters
US4097466A (en) * 1975-05-17 1978-06-27 Chemische Werke Huels Aktiengesellschaft Liquid coating compositions
US4997907A (en) * 1989-03-11 1991-03-05 Hoechst Aktiengesellschaft Curable powder mixtures
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5739213A (en) * 1995-01-06 1998-04-14 Shell Oil Company Acid functional and epoxy functional polyester resins
US5811198A (en) * 1995-01-06 1998-09-22 Shell Oil Company Acid functional and epoxy functional polyester resins
US6107442A (en) * 1997-02-21 2000-08-22 Shell Oil Company Outdoor durable coating compositions and acid functional polyester resins and polyglycidyl esters thereof usable therefor
US6187875B1 (en) 1997-03-25 2001-02-13 Shell Oil Company Acid functional polyester resins and lower temperature curable powder coating compositions comprising them
WO2010121392A1 (en) * 2009-04-21 2010-10-28 Dow Global Technologies Inc. Thermosettable composition containing a half ester of a cycloaliphatic diol and a thermoset product therefrom
EP2421907A1 (de) * 2009-04-21 2012-02-29 Dow Global Technologies LLC Wärmehärtbare zusammensetzung, enthaltend einen halbester eines cycloaliphatischen diols und wärmeghärtetes produkt daraus
US8691920B2 (en) 2009-04-21 2014-04-08 Dow Global Technologies Thermosettable composition containing a half ester of a cycloaliphatic diol and a thermoset product therefrom
EP2421907B1 (de) * 2009-04-21 2016-11-23 Dow Global Technologies LLC Wärmehärtbare zusammensetzung, enthaltend einen halbester eines cycloaliphatischen diols und wärmeghärtetes produkt daraus

Also Published As

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JP3432278B2 (ja) 2003-08-04
JPH0725990A (ja) 1995-01-27
KR950003344A (ko) 1995-02-16
EP0634434B1 (de) 2002-01-30
DE69429746T2 (de) 2002-08-08
DE69429746D1 (de) 2002-03-14
EP0634434A3 (de) 1995-05-24
KR100327917B1 (ko) 2002-07-06
TW315376B (de) 1997-09-11
CA2127966A1 (en) 1995-01-16
EP0634434A2 (de) 1995-01-18

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